Ethyl isovalerate → HCID 14033523, compound

HRID 1086061Notes

Reaction equation

HRID 1086061 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12].[F:18][C:19]1[CH:33]=[CH:32][C:22]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1>O1CCCC1>[F:18][C:19]1[CH:33]=[CH:32][C:22]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)([OH:24])[CH:10]([CH:11]([CH3:13])[CH3:12])[C:9]([O:15][CH2:16][CH3:17])=[O:14])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7945Ethyl isovalerateHCID 95824,4'-DifluorobenzophenoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 14033523HCID 14033523, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Lithium diisopropylamide (22.2mL of 1.8M solution, 40 mmol) was added to a solution of ethyl isovalerate (5.2g, 40 mmol) in 40 mL of tetrahydrofuran at -40° C. After stirring for 0.5 hours and cooling to -70° C., 4,4'-difluorobenzophenone (4.36 g, 20 mmol) was added and the mixture stirred for 3 hours during which time the temperature was allowed to warm to -20° C. The reaction was quenched with 1N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 5.3 g of the title product; m.p. =118°-120° C.

Workup

  1. stirringthe mixture stirred for 3 hours during which time the temperature
  2. temperatureto warm to -20° C
  3. customThe reaction was quenched with 1N hydrochloric acid
  4. extractionthe mixture extracted with diethyl ether
  5. dry with materialThe extracts were dried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-0f212ca6a1db46f39f9a5b52377387c8
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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